Baby Girl and Naughty Boy Ch. 08

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"Yes, I most certainly do. Very much." I replied.

"She loves you, too." Angie continued. "Just so you know, she and I spoke on the phone about you for several hours and, just about every other thing she said was about how wonderful you were and how much she loves you."

That made me feel good, and as I reflected on what Angie said, I got this warm feeling in my chest. But that warm feeling faded when Angie spoke again.

"Paul," she said, "come over here and stand in front of me, please."

Slowly, I stood up and took the few steps until I was standing about three feet in front of her.

"Would you feel more comfortable with your clothes off, Paul?" Angie asked.

"What?" I answered.

"It's a simple question, Paul." She replied, as she took a step closer to me and placed her hand on my wrist. "I'm offering you a chance to take your clothes off."

"Uh, well..... I don't know. I wasn't expecting this." I said.

"Okay, then, let's try it this way," Angie continued, with a firmer voice this time, "I want you to take your shoes, shirt and pants off."

I looked at Angie and while she moved her hands to her hips as she stood across from me, she spoke again. "Paul, you're asking me to help you and I'm trying to do that. Take your clothes off so we can get started."

Without knowing why, I kneeled down and untied both of my shoes and took them off. Then reaching up to unbutton my shirt, I felt the bra under my shirt and I started to panic. Angie probably sensed my hesitation because she got my attention by saying, "Paul, I'm waiting. Take your shirt and pants off so I can see you. Please don't make me ask again. I don't want to resort to other methods."

My fingers resumed their task of unbuttoning my shirt, and when I finished, I looked at Angie. "That's good, Paul. Now take it off and hand it to me."

I held my shirt closed as I looked at her. After a second, she shook her head in disbelief, took a step toward me and reached up to pull the flaps of my shirt open and slide it down my shoulders. I felt like a child being undressed by his mother at the doctor's office.

As my shirt slipped away, my arms automatically moved to cover my chest, trying to hide the fact I was wearing a bra from her. "Put your arms down." Angie said softly.

When I lowered my arms, she moved right in front of me and reached up to straighten the bra's shoulder straps and then she placed both her hands over my bra cups. "Paul, does it make you uncomfortable for me to see you like this? With a bra on?" She asked.

I couldn't speak. I tried to say something, but my mouth was dry.

"Paul?" Angie said. "Please answer me."

I shook my head and cleared my throat. "No, I'm not uncomfortable." I answered.

"No," Angie replied, "I wouldn't think so, either. You should be used to wearing lingerie by now. But, something's making you uneasy, isn't it? Tell me what it is."

"Uh, it's just that I wasn't really expecting to have to undress today. Patty said we were just going to talk." I said.

"No Paul," Angie said quickly, "you're not being very honest with me. Now, I'll ask again. Tell me why you're not cooperating. Tell me the truth this time."

I felt myself blush and a hot flash spread across my cheeks and chest. Angie was very perceptive and I don't know how she knew I was lying. It wasn't the fact that I was standing in front of her with a bra on, or even the fact that I was wearing those silky, ruffled panties under my pants that made me uneasy.

"I'm hard." I mumbled.

"I'm sorry," she said as she looked up into my face, "Speak up, Paul. I didn't hear you."

"I'm hard." I repeated. "I've got an erection."

"And you know that when you take your pants off, I'm going to see your erection inside your panties and you're afraid I'll think this is sexually exciting for you. Is that right?" Angie cut right to the quick.

I nodded my head up and down.

"Honestly, I would be worried if you weren't sexually excited, Paul. You're a full grown man who's about to undress yourself and stand in front of me in only a bra and a pair of sexy panties. Believe me, I can fully understand why you're cock is hard." She said softly, as she searched for my nipples through the bra cups. "Now, quit wasting time and do as I asked. Undo your pants and let them fall to the floor so I can see you properly."

Mysteriously, my hands followed her instructions. I unfastened my belt, undid my pants and let them drop. I couldn't bear to look at her so I turned my face away and stared at the wall across the room. Angie took a step backwards and looked at me. "I like them." She said, referring to the ruffled bridal panties I was wearing. "They're nice and girly. Tell me, Paul, do you like them?"

I managed to croak out a "Yes".

"I bet you do." Angie added. "You like them because they make you feel feminine. Isn't that right? They have those cute ruffles on the back and you love the way they feel. Say it Paul, admit it out loud to me." She urged.

Her words caused me to think, and when I didn't answer quick enough, Angie said, "Paul, we're never going to get anywhere if you don't open up to me. There's no one here but you and me. So, go ahead and answer my question. I think I've been very patient with you so far, but my patience is running out."

"Yes," I mumbled, "I like them. I like the way they look and the way they feel."

"You didn't answer my question, Paul." She replied. "I asked you if you liked them because they make you feel feminine. Tell me if I'm wrong about that."

"Uh," I began, "no, you're not wrong. It's just that, uh, well...."

"Go on," she said, "I'm listening."

"It's just that it's hard to stand here like this and admit it to, uh..... a woman." I answered. "Most women aren't very forgiving towards a man wants to dress like this."

"Good. Now we're finally getting somewhere." She said, smiling softly at me. Angie held out her hand and helped me step out of the pants that were puddled around my ankles. Once my feet were free, she sat down on her couch and pulled me to stand in front of her.

"Tell me," she began, "do you like females, Paul? Do you get hard, maintain an erection, and feel sexually gratified after you've had sex with a female?"

"Yes." I replied.

"That's because you have a typical male sex drive, Paul." She added. "And deep inside your head, you know you'll get the sexual gratification you need as a man by sexually interacting with a female. Does that make sense to you?"

I nodded my head up and down and told her it made sense.

"The problem is," Angie said, as she grasped my hands gently and pulled my bra and panty clad body closer to her, "for you it's not that simple. When you were young, your mother dressed you in girl's panties. By doing that, she planted the seeds of a gender conflict in your young brain. As you got older, you learned to get sexual gratification from wearing girl's clothes and over time, your mother reinforced that behavior by giving you your own panties and letting you have her worn panties to masturbate with. In effect, she trained you to associate female clothing with sexual pleasure. And then, in your quest to experience more intense pleasure, you role played and emulated a young girl, and you've been doing it ever since."

She went on, saying, "Outwardly, you want to be a man and be able to take advantage of your male sex drive. But, there's a part of you that is infatuated with being a girl, and now that you're grown up, the girl in you is ready to be sexually active."

"So," Angie said, "the conflict you're having is the struggle between the man and the girl in you. If you want the conflict to go away, you either have to reject one, or accept them both. It's that simple"

"Paul, I see this dilemma routinely with my clients, and it's totally explainable." Angie added. "You have all the classic behaviors, mannerisms and desires of a 'Sissy', which is a man that derives sexual pleasure from dressing and acting as a pre-adult girl."

"It probably started around puberty," she went on, "and I'm betting you've always been attracted to submissive and humiliating fantasies, female cross-dressing and you've probably even had an overwhelming desire to have sex like a female, since most Sissies are bisexual."

Angie paused for a second and looked at me. She scooted forward on the couch and reached forward to place her hands on the front of my panties, pressing her hand against my hard cock. Then, looking up at me, she continued to speak.

"As I understand it, your mother dressed you up as her daughter and you had intimate contact with her while you were dressed like that. I'm sure all this made a huge impact on your sexual development, but, when you couldn't go to the next level and actually perform sexually as a female, it left you empty and wanting more. You had no choice but to fend for yourself and live out your desires secretly while you existed as a man."

As Angie spoke, she was lightly caressing my hard cock inside my panties and running her hands over my butt, feeling the delicate ruffles. When she looked up at me as she stopped talking, she had a gentle smile on her face. "Paul, you're a Sissy. It's as simple as that." She said.

Angie explained more about Sissies and in the space of an hour, Angie had put into words and fully described the conflict that had filled my life from the time I was a young kid. "Shit." I sighed. "Everything you've said makes sense."

"Patty told me you had a girl name you use. Your sister's name I think. What was it again?" Angie asked.

"Sissy." I answered. "I always called her Sissy."

"Well, that's somewhat appropriate, don't you think?" Angie replied as she smiled up at me. Then, continuing to smile, she said, "Slip your panties down for me, Sissy."

As my hands went to the waistband of my panties, Angie sat back and told me to lower them to my knees, adding, "I don't want you to take your panties off, they look way too cute on you. I just want you to display your cock to me."

I slid my panties down my thighs and left them there. When my cock pulled free of the silky garment, it bounced and waved back and forth in front of her. Seeing my hard tool sticking out in front of me, she leaned forward and took my member in her hands and stroked it slowly. "You've got a magnificent cock, Sissy." Angie whispered up to me. "I see so many that aren't even half this big. It's nice to feel a big, hard one for a change."

I could tell that Angie knew how to stroke a cock. I guess in the same way a man doesn't know exactly how to touch a woman perfectly, so many women don't know how to touch a man perfectly. But Angie, just like Patty, knew how to handle a man's prick. She used a combination of squeezing and stroking to bring a drop of precum to the tip of my cock. Then touching her finger to the drop, she held her hand up to me and said, "Suck."

I bent down and took her finger into my mouth and sucked. "Very good, Sissy." Angie said. "Now, I want you to pay attention again."

Angie told me I needed to accept the fact that I was an honest-to-goodness Sissy -- part man, and part girl. "You can be manly when you want to, and be a Sissy when you want to. That's the beauty of being a Sissy, Paul. You can choose when you're going to be your Sissy persona." Then she added, "But, you have to fully accept it as the way you are and you have to quit fighting it. It will touch every part of your life, and if you'll just learn to accept it, you can control it instead of it controlling you."

"There's something else you need to know." Angie said as she worked another drop of precum up to the tip of my cock and then offered it up to me. As I sucked the sticky precum off her finger, she let go of my cock and stood up to face me. "You're going to have to face the fact that you're bisexual. You know that's true -- it has to be if you're really a Sissy. As a man, you're going to want to have sex with women the normal way you always have, by using your cock. But when you're a Sissy, you're going to want to have a cock. And from what Patricia's told me, I think you've already realized that."

Angie explained to me that in all her years of being a Domme, she's learned that the hardest thing for a Sissy to accept is that they are bisexual. She said a Sissy who can't admit they are bisexual will spend their whole life trying to convince them selves they aren't. She urged me to accept it and realize it was part of who I was. Along with that, I had to accept the fact that my interest in sucking cock and taking one in my butt was going to be something I would have to manage responsibly.

"Sissy," she said, "I want you to repeat after me. Whatever I say, I want you to repeat it back to me. Can you do that?"

I nodded my head and said I would. "Good," she replied, "let's try it."

"I am a Sissy." Angie said out loud. Then added, " I'm bisexual and I'm not ashamed of it."

I knew what she was up to. She was using a well known self-confidence technique to get me to say those words, hoping that once I'd said them, I would start to believe them. And while I thought it was a little trite and demeaning to make me repeat after her, I recognized the need for me to say those words out loud.

"I'm a Sissy," I said, "I'm bisexual and I'm not ashamed of it."

"Again," Angie said, "but this time like you mean it."

So I said it again, this time a little louder. Then she had me do it again, and again and again until I was almost shouting it. "Very good," Angie praised me, "I want you to do that three times every day for a month while you're looking in the mirror."

"Now, there's another matter to consider." Angie said, with a serious tone to her voice. "Patricia."

So far, I completely understood everything Angie was saying and as far as I was concerned, I believed she was really trying to help me. But, when she brought up Patty, I went into a tail spin.

Angie reached out and took my hand and placed it on my cock. "Stroke yourself, Sissy. But, don't cum or I'll have to punish you. And believe me, I mean that."

Once I started jacking myself, she sat on the couch again, leaned back, crossed her legs and watched me. After two or three minutes, I slowed down because I started to feel like I was getting close to cumming. "I can help you learn to throttle your excitement, Paul." Angie added. "Most Sissies have a bit of an exhibitionist in them, and you'll be tempted to display yourself while you're being a Sissy. The only thing is, once you have your climax and your excitement is over, it's common to feel regret, shame and humiliation over your actions. You have to learn to slow down and be in charge of your emotions and your cock. Don't let the little head control the big head, Sissy."

I slowed my stroking down even more and loosened the grip on my pole as my hand rubbed up and down. "Now," she said, "what are we going to do about Patricia?"

"I should probably talk to her and tell her what we talked about." I answered.

"Oh, I like that idea, Sissy. I like it very much. And what would you tell her?" Angie asked.

I started to list it all off, starting with the fact that I was a Sissy, I was bisexual, that I loved Patty and that I wanted her to accept me as a Sissy and as a Man. I also said I wanted Patty to help me be a good Sissy and I wanted her to be my partner in this.

"All that is just perfect, Sissy!" Angie complimented me. "There's one thing I might suggest, though. A Sissy really needs a mother figure to take charge sometimes -- to give you direction, permission, discipline and training. If you really love Patricia and want her to be your Sissy partner, you should probably ask her to be your 'Mommy'."

She had a damn good point, and it seemed like a good idea especially since Patty had already assumed that role the night she made love to my virgin ass with her strap-on.

"Stop stroking, Sissy." She ordered. "There are a couple more things I want to tell you and then I'm going to have you do something nice for Patricia."

She pointed down to my seriously leaking cock. "A good Sissy always cleans herself up. That means with your mouth. It also means no hesitation, no stalling and no complaints. And not only do you have to clean yourself, but you have to clean your Mommy, and anyone she asks you to clean. That's just part of being a Sissy and you'll learn to love it, believe me. Even if you have to clean up someone else's cum from your Mommy's pussy, you'll gladly do it, I assure you."

"And speaking of that," she said, "I hope you're ready to accept a submissive role when you're in your Sissy persona. That's your place now, submissive to your Mommy. When you're not being a Sissy, then you don't have to be submissive if you don't want to. But, when ever you're playing your Sissy role, your Mommy should always look out for you. You should always mind her, never question her and always respect her wisdom and abide by her wishes."

"Here's the kicker that goes with that." Angie explained. "Listen closely and make sure you heed the implied warning here. When you're in your Sissy role, you have no right to expect your Mommy not to have other sexual partners. You better be damn good and ready to let her have other men or women. You could be expected to help get the man hard, put his cock in her and then stand to the side and watch her have sex. Then afterwards, you could be asked to clean them both up. If you can't do that, then perhaps you're going to have to be a Sissy without a Mommy. What I want you to do is talk to Patricia about it soon -- like tonight or tomorrow and get all this decided ahead of time. She's had exposure to Sissies before, so she'll know to expect a discussion like this."

I told her I understood all that. I confided in her that I was hoping to be the one to take her virginity. It was difficult to accept, but I told Angie I would allow Patty to have the pleasure she wanted, and if that meant other men or women, I wouldn't put up a fuss. Angie told me most Sissies enjoyed cleaning up their Mommies after she had sex, and she suspected I wouldn't be any different. "It's something you'll look forward too, I imagine." She added.

"I'm not saying she'll use this as an excuse to look for other partners," Angie said, "all I'm saying is that it's part of the Sissy lifestyle and you better be aware of that. Honestly, based on what she's told me, I'm betting the two are going to be pretty exclusive to each other."

I was glad to hear that, for sure.

"Lastly, I want you to think about the way you are dressed right now. Not the fact that you're in your bra and panties, but the fact that you're panties are pulled down." She said. "I tell all my Sissies to get used to being seen like that. Some Mommies will want to show their Sissies off. Sometimes it's for their own enjoyment, maybe sometimes because they're proud of you. Sometimes it might be to embarrass or humiliate you, especially if you've been a bad Sissy. So not only do you have to be ready to be dressed in anyway they ask, including lingerie and any female attire, but, you have to be ready to lower your panties if she asks you to. Not all the way off, remember. Just be ready to quickly lower them to your thighs or your knees and don't ever cover up. In your Sissy role, your Mommy makes decisions for you and she has the right to dress you or undress you in any way she pleases, and that includes exposing you. When you to lower your panties, you're acknowledging your submissiveness to her. It's a sign of respect."

Angie and I talked for a while longer and while we did, I cleaned the drippings from my cock just the way she taught me. She finally stood up and came close to me and hugged me. "Paul, you're going to be a fine Sissy, I know you are. And Patricia will be a wonderful Mommy for you. I hope you'll think about coming to see me for a day or two sometime in the future - no charge, of course, so I can train you on some of the finer points of being a Sissy. Patricia has some knowledge of Sissification, so I'm sure she'll help you, too. And that brings me to almost the last thing we need to do."